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Lamininyl oxalamide with anticancer activity and its synthesis method and application

A technology of lamininate-based oxamide, which is applied in the field of lamininate-based oxalamide and its synthesis, can solve the problems of NIK-3T3 toxicity and other problems, and achieve the effect of expanding high value-added applications

Inactive Publication Date: 2020-08-14
QINGDAO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, researchers have screened and developed the anti-tumor activity of algae in the coastal area of ​​Shandong. Although the extract of Ulva ulva has high cytotoxic activity against human coelomoma KB cells and HT-29 cells, it is also effective against normal human cells. Cell NIK-3T3 also has greater toxicity

Method used

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  • Lamininyl oxalamide with anticancer activity and its synthesis method and application
  • Lamininyl oxalamide with anticancer activity and its synthesis method and application
  • Lamininyl oxalamide with anticancer activity and its synthesis method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0027] (1) Synthesis of 6-N,N,N-trimethyl-2-carbamoylamide hydrochloride: Reflux 10mmol (2.24g) lamininine hydrochloride in thionyl chloride for 2h, add Dissolve 10mmol of methylamine (0.33g) in 20mL of tetrahydrofuran (THF) solution, continue to reflux for 5h, evaporate the excess solvent, adjust the pH value to neutral with dilute hydrochloric acid, a white precipitate precipitates, filter, and wash with ice ethanol, After washing with diethyl ether several times and drying in vacuo, 1.51 g of a white solid product—6-N,N,N-trimethyl-2-carbamoylamide hydrochloride was obtained, with a yield of 64.1%;

[0028] (2) Synthesis of lamininic acid ester oxalamide: 27 mmol (6.96 g) of N-(2-hydroxynaphthylamino) oxalyl ethyl ester was dissolved in 30 mL of absolute ethanol solution, and slowly Add it dropwise to anhydrous THF dissolved with 32mmol (7.58g) of 6-N,N,N-trimethyl-2-carbamoylamide hydrochloride to maintain the reaction for 60min, then raise the temperature to 60°C and heat...

Embodiment 2

[0031] (1) Synthesis of 6-N,N,N-trimethyl-2-carbamoylamide hydrochloride: Reflux 10mmol (2.24g) lamininine hydrochloride in thionyl chloride for 3h, add Dissolve 10mmol of methylamine (0.33g) in 20mL of tetrahydrofuran (THF) solution, continue to reflux for 5h, evaporate the excess solvent, adjust the pH value to neutral with dilute hydrochloric acid, a white precipitate precipitates, filter, and wash with ice ethanol, After washing with diethyl ether several times and drying in vacuo, 1.03 g of a white solid product—6-N,N,N-trimethyl-2-carbamoylamide hydrochloride was obtained, with a yield of 43.7%;

[0032] (2) Synthesis of lamininic acid ester oxalamide: 27 mmol (6.96 g) of N-(2-hydroxynaphthylamino) oxalyl ethyl ester was dissolved in 30 mL of absolute ethanol solution, and slowly added dropwise to anhydrous THF dissolved with 6-N,N,N-trimethyl-2-carbamoylamide hydrochloride with a molar ratio of 0.8 to maintain the reaction for 60 minutes, then heated to 30°C for 10 hour...

Embodiment 3

[0034] (1) Synthesis of 6-N,N,N-trimethyl-2-carbamoylamide hydrochloride: Reflux 10mmol (2.24g) lamininine hydrochloride in thionyl chloride for 8h, add Dissolve 10mmol of methylamine (0.33g) in 20mL of tetrahydrofuran (THF) solution, continue to reflux for 5h, evaporate the excess solvent, adjust the pH value to neutral with dilute hydrochloric acid, a white precipitate precipitates, filter, and wash with ice ethanol, After washing with diethyl ether several times and drying in vacuo, 1.03 g of a white solid product—6-N,N,N-trimethyl-2-carbamoylamide hydrochloride was obtained, with a yield of 55.3%;

[0035] (2) Synthesis of lamininic acid ester oxalamide: 27 mmol (6.96 g) of N-(2-hydroxynaphthylamino) oxalyl ethyl ester was dissolved in 30 mL of absolute ethanol solution, and slowly Added dropwise to anhydrous THF dissolved with 6-N,N,N-trimethyl-2-carbamoylamide hydrochloride with a molar ratio of 1.1 to maintain the reaction for 60 minutes, then heated to 90°C for 4 hours, ...

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Abstract

The invention discloses laminine ester based oxamide with the antitumor activity as well as a synthesis method and application thereof. The natural marine organism nonprotein-laminine is used for synthesizing the novel laminine ester based oxamide with antitumor activity; the high-added value application of natural marine resources is expanded; the cation property of the laminine salt is maintained by the laminine ester based oxamide; certain water affinity is realized; meanwhile, naphthalene rings of plane structures are implanted, so that the embedding of the protein molecules to attack thecancer cell targeted points is facilitated; in addition, through the implanting of ethylenedione diamine molecular structures, the mutual action of active center metal ions of bio-enzymes in the sametargeted point protein molecules is facilitated, so that the enzymes are inactivated; the apoptosis of the cancer cells is promoted; therefore the treatment is precise; the effect is better. In addition, through the use of in vitro cytotoxic activity experiments, the condition that the compound has the anticancer activity effect is proved; the laminine ester is suitable for being used in the fieldof anti-cancer medicine development; great medicine and pharmacy values are realized.

Description

technical field [0001] The invention relates to the technical field of drug synthesis and application, and more specifically relates to a lamininate-based oxalamide with anticancer activity and its synthesis method and application. Background technique [0002] At present, cancer is one of the main diseases that cause human death, killing more than 7 million people worldwide every year. It is estimated that the number of cancer deaths worldwide will continue to rise, and may exceed 13.1 million by 2030. About 30% of the new drugs that have been developed and marketed in the world are derived from natural products. In recent years, the research on natural anticancer drugs from terrestrial sources has not achieved many exciting new results. Therefore, people have turned their attention to the ocean. Discovery of new anti-cancer drugs from the ocean. [0003] Laminin is an active amino acid with anticancer and antihypertensive activities derived from the marine organism kelp. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C237/22C07C231/14A61P35/00
Inventor 李晓雯李子超李群高琪
Owner QINGDAO UNIV
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